Synthesis and characterization of molecularly imprinted polymers for recognition of ciprofloxacin

Abstract

A molecularly imprinted polymer (MIP), with special molecule recognition properties of ciprofloxacin (CIP), was prepared by thermal polymerization in which ciprofloxacin acted as template molecule, a-methacrylic acid (MAA) acted as functional monomer and trimethylolpropane trimethylacrylate (TRIM) acted as crosslinker. The optimized ratio was determined to be n(CIP): n (MMA):n(TRIM) 5 1:6:16 by investigation of the effects of different concentrations of functional monomer and the crosslinker on the MIP's recognition properties. Equilibrium binding experiment was used to investigate the adsorption dynamics, the binding ability to template molecule and the substrate selectivity. Scatchard analysis was used to study the MIP's binding characteristic to template molecule. The results indicated that MIP has higher adsorption ability and selectivity. The equilibrium distribution coefficient K D was 41.64 and the separation factor a was 1.62. Scatchard analysis showed that two different kinds of binding sites were produced in the polymer matrix and their dissociation constants were calculated to be K d 1 5 5.249 6 10 2 5 mol?L 2 1 , K d 2 5 2.237 6 10 23 mol?L 21 .Molecular imprinting technology (MIT) refers to the preparation of a polymer with special recognition properties of a specific target molecule (template molecule, imprinted molecule) [1]. Wulff [2] gave the first report of a synthetic molecularly imprinted polymer in 1972, and Mosbach [3] issued a molecularly imprinted polymer of theophylline which was prepared under the intermolecular interaction principle in Nature in 1993. Since then the molecular imprinting technique started to develop flourishingly. Molecularly imprinted polymers prepared through MIT have many characteristics, such as high affinity and selectivity, strong ability in an anti-adverse environment, good stability, long service life, wide application range and so on; they have been used in many fields, including chromatographic analysis [4,5], solid phase extraction [6,7], biosensors [8,9], membrane technology [10,11] and so on.Quinolones (QNs), which have undergone rapid development in the past 20 years, are a kind of important broad-spectrum antibiotics. They are used extensively for treatment, prevention and growth promotion [12]. As one of the most representative third-generation quinolones, ciprofloxacin has excellent antibacterial activity. Thus far, cyclopropyl has been considered as the best 1-substituent. This change in structure is significant in the history of the development of quinolone antibiotics [13]. Close attention has been widely paid to the residue problem, such as drug resistance of pathogenic bacteria and potential carcinogenicity of some quinolones [12][13][14], but it is difficult to analyze the residue of QNs accurately due to severe matrix interferences and low levels of drug residue. The authors wish, through this paper, to achieve the elimination of matrix interference and establish effective purification by using MIP with special recognition properties. Caro and Mar...

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

“…The demonstration of template (or template analog)‐selective recognition by an MIP remains a cornerstone in the development of all new MIP systems. Various strategies have been employed to characterize ligand‐polymer binding events,…”

Synthesis of Atenolol-Imprinted Polymers with Methyl Methacrylate as Functional Monomer in Propanol Using Bulk and Precipitation Polymerization Method

“…The evaluation of NIP was carried out by the same procedure as that for MIP. The imprinting factor was calculated using the following equation:KD=Ci−CfVCfm,IF=KD MIPKD NIP,where K D is the distribution coefficient; C i and C f are the concentration of atenolol before and after the adsorption experiments, respectively; V is the volume of solution containing atenolol; and W is the weight of the polymer [13, 14].…”

Microsphere Polymers in Molecular Imprinting: Current and Future Perspectives

“…The crosslinker in the RAFTPP technique has a lower ratio towards the template and monomer compared to precipitation polymerisation. Liu et al [ 141 ] explained that less crosslinker will create long, free polymer chains within large pore diameters and low mass transfer resistance due to fewer crosslinking sites. Another result from Barros et al [ 142 ] shows that a large amount of functional monomer typically results in more non-specific interaction sites.…”

“…The mixture has to reach room temperature before being admitted to the flask at 400-600 rpm under a gentle stream (about 60 bubbles per minute) of nitrogen (99.99%). The temperature is then raised to 60-70 °C for the polymerisation process for 24 h. The microspheres have to be washed with a combination of distilled water, methanol and acetic acid [110,120], ethanol [80] or acetone [141]. The ratio between monomers and molecule template must be adjusted-too many or too few monomers will affect the affinity and selectivity of the polymer formed; this was examined by Shi [120] with five different monomer to molecule target ratios of 2:1, 3:1, 4:1, 6:1 and 8:1.…”

“…The effect of the amount of surfactant or suspending agent on the size and distribution of particles has also been assessed. A higher amount of surfactant produces smaller average particle diameters and a narrower size distribution [141]. Gluten and PEG 4000 at 4%, and PVA1788 at 2%, The reason for the adjustment ratio for the monomer to molecule template has been explained [81].…”